CA2763773A1 - Antimicrobial polymers - Google Patents

Antimicrobial polymers Download PDF

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Publication number
CA2763773A1
CA2763773A1 CA2763773A CA2763773A CA2763773A1 CA 2763773 A1 CA2763773 A1 CA 2763773A1 CA 2763773 A CA2763773 A CA 2763773A CA 2763773 A CA2763773 A CA 2763773A CA 2763773 A1 CA2763773 A1 CA 2763773A1
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Canada
Prior art keywords
polymer
group
monomer
hydrophilic
integer
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Abandoned
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CA2763773A
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French (fr)
Inventor
Gregory N. Tew
Ahmad E. Madkour
Karen Lienkamp
Ashlan Marie Musante
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University of Massachusetts UMass
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University of Massachusetts UMass
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Publication of CA2763773A1 publication Critical patent/CA2763773A1/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
    • C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D225/06—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Public Health (AREA)
  • Communicable Diseases (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Furan Compounds (AREA)

Abstract

The invention generally relates to novel polymers (SMAMPs) and their syntheses and use. The polymers exhibit promising properties of AMPs, In particularly, for example, a ring-opening metathesis polymerization (ROMP) platform was developed that allows syntheses of SMAMPs that employ a minimum number of norbornene-based building blocks and/or enable easy and independent variation of hydrophobic and hydrophilic groups in the monomer units and/or along the polymeric backbone to finetune and select desirable properties of the polymers.

Claims (46)

1. A monomer unit having the structure of:

wherein one of R1 and R2 comprises a hydrophobic group and the other one of R1 and R2 comprises a hydrophilic group; and X is C-R3, O or S, wherein R3 is a hydrogen or a C1-C12 alkyl or alkoxy group.
2. The monomer of Claim 1, wherein the hydrophobic group comprises a substituted or unsubstituted alkyl group.
3. The monomer of Claim 2, wherein the hydrophobic group is a substituted or unsubstituted C1-C10 alkyl group.
4. The monomer of Claim 1, wherein the hydrophilic group is cationic
5. The monomer of Claim 1, wherein the hydrophilic group comprises a group selected from ammonium ions, sulfonium ions, guanidinium ions, phosphonium ions, and mono-and di-alkyl substituted amino groups.
6. The monomer of Claim 5, wherein the hydrophilic group is a guanidinium ion.
7. The monomer of Claim 1, wherein X is O; R1 is a linear or branched C1-C12 alkyl group;
and R2 is or a guanidinium ion wherein p is an integer from 1- 10.
8 The monomer of Claim 1, wherein both -C(=O)O- groups in (1) occupy the exo-stereo position.
9. The monomer of Claim 7, wherein R1 is a linear or branched C1-C6 alkyl group; and p is an integer from 1 - 5.
10. The monomer of Claim 1, wherein X is C-R3; R1 is a linear or branched C1-C12 alkyl group; and R2 is or a guanidinium ion, wherein p is an integer from 1 -10.
11. The monomer of Claim 10, wherein R3 is hydrogen.
12. A polymer comprising a monomer unit having the structure of:
wherein one of R1 and R2 comprises a hydrophobic group and the other one of R1 and R2 comprises a hydrophilic group; and X is C-R3, O or S, wherein R3 is a hydrogen or a C1-C12 alkyl or alkoxy group.
13. The polymer of Claim 12, wherein the hydrophobic group comprises a substituted or unsubstituted alkyl group.
14. The polymer of Claim 13, wherein the hydrophobic group is a substituted or unsubstituted C1-C10alkyl group.
15. The polymer of Claim 12, wherein the hydrophilic group is cationic.
16. The polymer of Claim 12, wherein the hydrophilic group comprises a group selected from ammonium ions, sulfonium ions, guanidinium ions, phosphonium ions, and mono-and di-alkyl substituted amino groups.
17. The polymer of Claim 12, wherein the hydrophilic group is a guanidinium ion.
18. The polymer of Claim 12, wherein X is O, R, is a linear or branched C1-C12 alkyl group;
and R2 is or a guanidinium ion, wherein p is an integer from 1-10.
19. The polymer of Claim 12, wherein both -C(=O)O- groups in (II) occupy the exo- stereo position.
20. The polymer of Claim 18, wherein R1 is a linear or branched C1-C6 alkyl group, and p is an integer from 1 - 5.
21. The polymer of Claim 12, wherein X is C-R3; R1 is a linear or branched C1-C12 alkyl group; R2 is or a guanidinium ion, wherein p is an integer from 1-10
22. The polymer of Claim 21, wherein R3 is hydrogen.
23. The polymer of Claim 12, wherein n is an integer from about 1 to about 1,000.
24. The polymer of Claim 23, wherein n is an interger about 1 to about 20.
25. The polymer of Claim 23, wherein n is an interger about 1 to about 10
26. The polymer of Claim 12, wherein the polymer is a co-polymer.
27. The co-polymer of Claim 26, wherein the co-polymer comprises the structural monomer units of:

wherein each of X' and X" is C-R3, O or S, wherein R3 is a hydrogen or a C1-C12 alkyl or alkoxy group;
each of R1' and R1" is a hydrophobic group and each of R2' and R2" is a hydrophilic group, provided that R1' and R1" are not the same, R2' and R2" are the same, or X' and X"
arc not the same; and each of m and n is an integer from about 1 to about 1,000.
28. The polymer of Claim 27, wherein each of m and n is an interger about 1 to about 20.
29. The polymer of Claim 27, wherein each of m and n is an interger about 1 to about 10.
30. The polymer of Claim 27, wherein the hydrophilic group is cationic
31. The polymer of Claim 27, wherein the hydrophilic group comprises a group selected from ammonium ions, sulfonium ions, guanidinium ions, phosphonium ions, and mono-and di-alkyl substituted amino groups
32. The polymer of Claim 27, wherein the hydrophilic group is a guanidinium ion.
33. The polymer of Claim 27, wherein all -C(=O)O- groups in (III) and (IV) occupy the exo-stereo position.
34 The co-polymer of Claim 27, wherein each of R1' and R1" is independently a linear or branched C1-C12 alkyl group;
and each of R2' and R2" is independently or a guanidinium ion, wherein p is an integer from 1 - 10.
35. The co-polymer of Claim 34, wherein each of X' and X" is O.
36. The co-polymer of Claim 34, wherein each of X' and X" is independently C-R3.
37. The co-polymer of Claim 34, wherein one of X' and X" is O and the other is
38 The co-polymer of Claim 34, wherein each of R1' and R1" is independently a linear or branched C1-C6 alkyl group.
39. The co-polymer of Claim 34, wherein p is an integer from 1-5.
40. A polymer prepared by ring-opening metathesis polymerization, the polymer comprising hydrophobic and hydrophilic groups attached to the polymeric backbone such that, within a monomeric structural unit, the hydrophobic and hydrophilic groups are attached to the polymeric backband at adjacent atoms.
41. The polymer of Claim 40, wherein the the hydrophobic and hydrophilic groups are attached to the polymeric backband via ester linkages.
42 The polymer of Claim 40, wherein the the hydrophobic group comprises a linear or branched C1-C12 alkyl group; and the hydrophilic group comprises a -NH3' group
43. The polymer of Claim 42, wherein the hydrophilic group comprises or a guanidinium i on, wherein p is an integer from 1 - 10.
44. The polymer of Claim 40, wherein the polymer is a co-polmer.
45. A product comprising the polymer of any of Claims 12-44.
46. A method for preparing a polymer of any of Claims 12-44 by ring-opening metathesis polymerization.
CA2763773A 2009-06-08 2010-06-08 Antimicrobial polymers Abandoned CA2763773A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US18503509P 2009-06-08 2009-06-08
US61/185,035 2009-06-08
PCT/US2010/037685 WO2010144386A2 (en) 2009-06-08 2010-06-08 Antimicrobial polymers

Publications (1)

Publication Number Publication Date
CA2763773A1 true CA2763773A1 (en) 2010-12-16

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US (2) US8153739B2 (en)
EP (1) EP2440540A4 (en)
JP (1) JP2012529557A (en)
KR (1) KR20120068806A (en)
CN (1) CN102596925A (en)
AU (1) AU2010258956A1 (en)
BR (1) BRPI1010997A2 (en)
CA (1) CA2763773A1 (en)
IL (1) IL216869A0 (en)
MX (1) MX2011013305A (en)
WO (1) WO2010144386A2 (en)

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US20180327607A1 (en) * 2015-11-18 2018-11-15 Albert-Ludwigs-Universität Freiburg Polymer having antimicrobial and/or antifouling properties

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EP2471827B1 (en) * 2010-12-30 2013-09-04 Universitätsklinikum Freiburg Covalently attached antimicrobial polymers
EP2636693A1 (en) 2012-03-09 2013-09-11 Universitätsklinikum Freiburg Synthesis and micro-/nanostructuring of surface-attached crosslinked antimicrobial and/or antibiofouling polymer networks
US9999633B2 (en) 2013-04-09 2018-06-19 International Business Machines Corporation Antimicrobial cationic polycarbonates
US9357772B2 (en) 2013-04-09 2016-06-07 International Business Machines Corporation Antimicrobial cationic polycarbonates
US9598543B2 (en) 2014-05-30 2017-03-21 Pall Corporation Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (VIa)
US9441078B2 (en) * 2014-05-30 2016-09-13 Pall Corporation Self-assembling polymers—I
US9593219B2 (en) 2014-05-30 2017-03-14 Pall Corporation Membrane comprising self-assembled block copolymer and process for producing the same by spin coating (IIa)
US9604181B2 (en) 2014-05-30 2017-03-28 Pall Corporation Membrane comprising self-assembled block copolymer and process for producing the same by spray coating (IIc)
CN105646851B (en) * 2014-05-30 2018-02-23 天津大学 A kind of magnetic polymer and preparation method thereof
US9193835B1 (en) 2014-05-30 2015-11-24 Pall Corporation Self-assembling polymers—IV
US9616395B2 (en) 2014-05-30 2017-04-11 Pall Corportaion Membrane comprising self-assembled block copolymer and process for producing the same by spray coating (Ic)
US9593217B2 (en) 2014-05-30 2017-03-14 Pall Corporation Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (Va)
US9593218B2 (en) 2014-05-30 2017-03-14 Pall Corporation Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (IIIa)
US9328206B2 (en) 2014-05-30 2016-05-03 Pall Corporation Self-assembling polymers—III
US9592476B2 (en) 2014-05-30 2017-03-14 Pall Corporation Membrane comprising self-assembled block copolymer and process for producing the same by hybrid casting (IIb)
US9469733B2 (en) * 2014-05-30 2016-10-18 Pall Corporation Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (IVa)
US9592477B2 (en) 2014-05-30 2017-03-14 Pall Corporation Membrane comprising self-assembled block copolymer and process for producing the same by hybrid casting (Ib)
CN104003926B (en) * 2014-05-30 2016-06-15 天津大学 Based on the side chain type magnetic monomer of alkylammonium salt, polymer and its preparation method and application
US9765171B2 (en) 2014-05-30 2017-09-19 Pall Corporation Self-assembling polymers—V
WO2018091467A2 (en) * 2016-11-15 2018-05-24 Albert-Ludwigs-Universität Freiburg A simultaneously antimicrobial and protein-repellent polyzwitterion
CN108467475B (en) * 2018-03-08 2020-02-14 山西大学 Cyclic polymer and preparation method and application thereof
CN109364766B (en) * 2018-11-20 2021-10-29 上海谊帅实业有限公司 Preparation method of ZIF-8/PVDF-g-PAMPS film with sterilization and iodine adsorption performances
CN114213632B (en) * 2021-12-14 2023-08-22 济南大学 Preparation method and application of amphiphilic fluorine-containing copolymer membrane with protein adsorption resistance
KR20240035076A (en) * 2022-09-08 2024-03-15 서울대학교산학협력단 Antibaterial polymer and antibaterial polymer film

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US20060115448A1 (en) * 2004-08-18 2006-06-01 Tew Gregory N Amphiphilic polynorbornene derivatives and methods of using the same
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180327607A1 (en) * 2015-11-18 2018-11-15 Albert-Ludwigs-Universität Freiburg Polymer having antimicrobial and/or antifouling properties
US10889726B2 (en) * 2015-11-18 2021-01-12 Albert-Ludwigs-Universität Freiburg Polymer having antimicrobial and/or antifouling properties

Also Published As

Publication number Publication date
EP2440540A2 (en) 2012-04-18
US8153739B2 (en) 2012-04-10
WO2010144386A2 (en) 2010-12-16
IL216869A0 (en) 2012-02-29
JP2012529557A (en) 2012-11-22
KR20120068806A (en) 2012-06-27
MX2011013305A (en) 2012-01-12
US20100317870A1 (en) 2010-12-16
BRPI1010997A2 (en) 2016-08-09
WO2010144386A3 (en) 2011-05-26
US20120195849A1 (en) 2012-08-02
CN102596925A (en) 2012-07-18
US8445611B2 (en) 2013-05-21
EP2440540A4 (en) 2012-12-12
AU2010258956A1 (en) 2012-01-12

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Effective date: 20140610